Potassium Phosphate, Tribasic → HCID 89908428, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-6-(3-hydroxypiperidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 118.1, 60 mg, 0.130 mmol), pyrimidin-5-ylboronic acid (24.2 mg, 0.196 mmol), Pd2(dba)3 (2.388 mg, 2.61 μmol), 2-dichlohexylphosphino-2′-4′-6′-triisoprophylbiphenyl (XPhos, 4.97 mg, 10.43 μmol) and K3PO4 (83 mg, 0.391 mmol) were added to a MW vial. The vial was sealed, evacuated/purged with argon, and BuOH was added. The RM was stirred at 100° C. for 16 h. The RM was diluted with THF (1 mL), treated with Si-Thiol (Silicycle, 1.44 mmol/g, 45.3 mg, 0.065 mmol), filtered and the filtrate was evaporated off under reduced pressure to give a residue which was purified by preparative HPLC (Condition 12, 25% for 0.2 min then 25% to 55% in 12 min) to yield the title compound as a white solid. UPLC-MS (condition 1) tR=2.31 min, m/z=460.1-461.1 [M+H]+, m/z=458.2-459.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.21-1.39 (m, 2H) 1.56-1.65 (m, 1H) 1.77-1.86 (m, 1H) 2.63 (dd, J=11.86, 8.44 Hz, 1H) 2.75-2.84 (m, 1H) 3.25-3.38 (m, 1H) 3.43-3.55 (m, 2H) 4.74 (d, J=3.91 Hz, 1H) 7.37 (d, J=8.80 Hz, 2H) 7.86 (d, J=9.05 Hz, 2H) 8.19 (d, J=2.20 Hz, 1H) 8.80 (d, J=2.20 Hz, 1H) 9.08 (s, 2H) 9.21 (s, 1H) 10.30 (s, 1H).

Provenance & Evidence